Chemistry of sulfoxides and related compounds. XIII. Synthesis of 2-thiabicyclo[2.2.1]heptane derivatives

Johnson, Carl R.; Keiser, Jeffrey E.; Sharp, Joanne

doi:10.1021/jo01256a018

Cited by 41 publications

(10 citation statements)

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“…This could be rationalized in terms of a "W"-type long range coupling (15) between the anti-proton of the methylene bridge and H-5 and H-4 which, in this case, must be endo. Such long range couplings have been observed in several bicyclic systems (7,16). On this basis the A and B portions of the signal were assigned to the syn and anti protons of the methylene bridge, respectively.…”

Section: Resultsmentioning

confidence: 62%

Studies on the Synthesis of Novel Carbohydrates with Sulfur in the Ring. Part III. The Synthesis of Derivatives of 2,6-Dithio-hex-4-en-2-ulopyranosidononitriles

Vyas¹,

Hay²

1975

Can. J. Chem.

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The cis-hydroxylation of 3,6-dihydro-3-methoxy-2-methylthio-2H-thiopyran-2-carbonitrile and of 3-exo-cyano-3-methylthio-2-thiabicyclo[2.2.l]hept-5-ene by treatment with 0s04-pyridine afforded sulfur analogs of two new types of carbohydrates. The Diels-Alder reaction of trans,trans-l,4-diacetoxy-l,3-butadiene with methyl cyanodithioformate gave a one-step synthesis of methyl 3,6-di-0-acetyl-4,5-dideoxy-2,6-dithio-a-~~-threo-hex-4-en-2-ulopyranosidononitrile.

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Section: Resultsmentioning

confidence: 62%

Studies on the Synthesis of Novel Carbohydrates with Sulfur in the Ring. Part III. The Synthesis of Derivatives of 2,6-Dithio-hex-4-en-2-ulopyranosidononitriles

Vyas¹,

Hay²

1975

Can. J. Chem.

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“…There remained the problem of establishing the stereochemistry at C-3. The shielding of endo ring protons or those of endo methyl groups in norbornene and 2-thiabicyclo t2.2.1 lhept-5-ene systems as a consequence of the vinylic diamagnetic anisotropy (16) is well established (17)(18)(19)(20) in n.m.r. studies.…”

Section: Resultsmentioning

confidence: 99%

Methyl Cyanodithioformate as a Reactive Dienophile in Diels–Alder Reactions

Vyas¹,

Hay²

1971

Can. J. Chem.

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A Diels-Alder reaction between cyclopentadiene and methyl cyanodithioformate afforded ,a 60:40 mixture of the isomers 2a and b. The n.m.r. studies of these compounds and the products of LiAlH4 reduction, 3a and b, established that the major isomer, 2a, was 3-exo-cyano-3-methylthio-2-thiabicyclo-[2.2.l]hept-Sene, and that 3a was the corresponding 3-exo-aminomethyl compound.Une rCaction de Diels-Alder entre le cyclopentadiene et le cyanodithioformate de methyle conduit a un mClange 60:40 des isomeres 2a et b. Une Ctude r.m.n. de ces composes et des produits de reduction par LiAlH,, 3a et b, prouve que le produit majoritaire, 2a, est le cyano-3 exo mtthylthio-3 thia-2 bicyclo[2.2.l]heptene-5; le produit 3a est l'aminoethyl-3 exo correspondant.

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“…( 1 H: 500 MHz, 13 C: 126 MHz) at 25 C with tetramethylsilane (TMS) as internal standard, using the ppm scale. High resolution mass spectra (HRMS) were obtained aer high performance liquid chromatography (HPLC) with a mass spectrometer AutoSpec M from Micromass, current loop probe supply, positive ionization, ow ¼ 10 ml min À1 .…”

Section: Generalmentioning

confidence: 99%

“…Yield: 89% (20. General procedure for the synthesis of cyclopentenyl ethers (procedure A) 13 To a freshly dried solution of THF 21.0 mmol of the appropriate alcohol were added and then heated to reux for 30 min. Aer cooling to room temperature 2.0 equivalents of sodium hydride were added while cooling.…”

Section: Characterization Of Compoundsmentioning

confidence: 99%

“…Because it was envisioned to introduce aryl ether groups to yield templates 7c-f, we prepared the corresponding cyclopentenol ethers 4b-d via a different route by the reaction of 3 with tosyl chloride and sodium hydride under reux in tetrahydrofuran, following a previously reported procedure. 13 Ether 4d could have been prepared by the same procedure as 4a but the second procedure gave superior results. All products were puried by column chromatography before being further reacted with meta-chloroperoxybenzoic acid in dichloromethane to give the oxirane precursors (5) in moderate to good yields.…”

Section: Introductionmentioning

confidence: 99%

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4-Aminocyclopentane-1,3-diols as platforms for diversity: synthesis of a screening library

et al. 2014

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Trisubstituted cyclopentanes have a discrete shapely curvature. While the central ring of these compounds is devoid of rotatable bonds, the pseudo rotation of the cyclopentane ring leads to a desirable disruption of planarity. This is favorable for aqueous solubility and enables addressing of wide-ranging conformational space. The sp 3 -rich framework of 4-aminocyclopentane-1,3-diols offers stereochemically defined attachment points for substituents and renders these fragment-like molecules good platforms for molecular diversity. By using an established N-selective polymer-assisted acylation protocol, these scaffolds with natural product-like properties were transformed into a screening library by attachment of substituents at defined positions. Here we describe the synthesis and characterization of these molecular platforms and their use as starting points for the construction of an 80-member library of 4-amidocyclopentane-1,3-diol monoethers. Five of the compounds displayed cytotoxicity in a tumor cell line assay with IC 50 values in the low micromolar range. Results and discussion SynthesisKey components for assessing structural diversity in diversityoriented synthesis (DOS) were recognized by Spring et al. as (1) appendage diversityvariation in structural moieties, around a common core scaffold, (2) functional group diversityvariation in the functional groups introduced into the periphery, (3) stereochemical diversityvariation in the orientation of potential macromolecule-interacting elements and (4) skeletal (scaffold) diversity. 12 With the intention to generate a set of platforms for molecular diversity and subsequently ornament

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Chemistry of sulfoxides and related compounds. XIII. Synthesis of 2-thiabicyclo[2.2.1]heptane derivatives

Cited by 41 publications

References 0 publications

Studies on the Synthesis of Novel Carbohydrates with Sulfur in the Ring. Part III. The Synthesis of Derivatives of 2,6-Dithio-hex-4-en-2-ulopyranosidononitriles

Studies on the Synthesis of Novel Carbohydrates with Sulfur in the Ring. Part III. The Synthesis of Derivatives of 2,6-Dithio-hex-4-en-2-ulopyranosidononitriles

Methyl Cyanodithioformate as a Reactive Dienophile in Diels–Alder Reactions

4-Aminocyclopentane-1,3-diols as platforms for diversity: synthesis of a screening library

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